3-((Benzyloxy)methyl)cyclobutanone → HCID 57425851, compound

HRID 1727313Notes

Reaction equation

HRID 1727313 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[CH2:7]([O:14][CH2:15][CH:16]1CC(=O)C1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH2:1]=[C:2]1[CH2:4][CH:16]([CH2:15][O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 118198503-((Benzyloxy)methyl)cyclobutanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57425851HCID 57425851, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

In a 50 mL three-neck flask with t-BuOK (0.54 g, 4.8 mmol) and methyltriphenylphosphonium bromide (1.72 g, 4.8 mmol) inside, dry 1,4-dioxane was added under argon to give a yellow emulsion. This was heated to 40° C. for 30 min, after which time the mixture was cooled to 10° C. and a 1,4-dioxane solution of 3-(benzyloxymethyl)cyclobutanone (0.76 g, 4 mmol) was added drop by drop. The mixture was left stirring at 10° C. for 3 hr. Then the solvent was removed by rotary evaporator and the residue was dissolved in Et2O and H2O. The organic phase was separated and the aqueous phase was extracted with Et2O. The combined organic phase was dried over MgSO4 and the solvent was evaporated to dryness to give an oily product, which was purified by silica gel flash chromatography (Hexane: EtOAc=20:1) to give a colorless oil (0.48 g, 63%, Rf=0.79 (Hexane:EtOAc=3:1)). 1H NMR (CDCl3, 400 MHz): δ 2.36-2.48 (m, 2H), 2.52-2.64 (m, 1H), 2.72-2.84 (m, 2H), 3.48-3.50 (d, J=7.2, 2H), 4.53 (s, 1H), 4.74-4.77 (m, 2H), 7.2-7.4 (m, 5H). 13C NMR (CDCl3, 100 MHz): δ 29.82, 35.06, 73.26, 74.60, 106.52, 127.77, 127.88, 128.60, 147.34. MS (FAB): expected for C13H16O (M+H)+ 189.27. Found 189.12748. IR (neat) νmax 2921, 2853, 1720, 1676, 1453, 1272, 1113, 1071, 1027, 875, 737, 713, 698.

Workup

  1. customto give a yellow emulsion
  2. temperatureafter which time the mixture was cooled to 10° C.
  3. waitThe mixture was left
  4. customThen the solvent was removed by rotary evaporator
  5. dissolutionthe residue was dissolved in Et2O
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with Et2O
  8. dry with materialThe combined organic phase was dried over MgSO4
  9. customthe solvent was evaporated to dryness
  10. customto give an oily product, which
  11. customwas purified by silica gel flash chromatography (Hexane: EtOAc=20:1)
  12. customto give a colorless oil (0.48 g, 63%, Rf=0.79 (Hexane:EtOAc=3:1))

Sources & evidence

ORD record
ord-235a7d06693b4befa5bcbcb5d7bdd4f3
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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